Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, belongs to pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 173253-42-4, Application In Synthesis of 2-Amino-5-bromo-6-chloropyrazine

To a solution of 5-bromo-6-chloropyrazin-2-amine (0.600 g, 2.8 mmol, 1 eq.) and benzo[d]thiazol-6-ylboronic acid (0.412 g, 2.3 mmol, 0.8 eq.) in dioxane (8 mL) and water (2 mL) was added Na2CO3 (0.549 g, 5.18 mmol, 2 eq.). The reaction was purged with N2 and PdCl2(dppf)?DCM complex (0.117 g, 5 mol %). The reaction mixture was deoxygenated using N2 atmosphere and the reaction mixture was heated at 100 C. for 16 h under microwave irradiation. The reaction was monitored by TLC and LCMS The reaction mixture was diluted with water and extracted with ethyl acetate (3*100 mL). The separated organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by normal phase column chromatography to afford desired product (0.210 g, 28%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-5-bromo-6-chloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-01-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 l) and NaOH (6 mol/l in water; 240 mL; 1.44 mol) is refluxed for 3 h.The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 mL). Water (200 mL) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60° C. Yield: 99.6 g (107percent of theory) C5H5ClN4O2 .ESI Mass spectrum: m/z=189 [M+H]+; m/z=187 [M-H]-

The chemical industry reduces the impact on the environment during synthesis Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; HECKEL, Armin; KLEY, Joerg; US2013/316981; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 957230-70-5,Some common heterocyclic compound, 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, molecular formula is C4H3Br2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 3,6-dibromo-pyrazin-2-ylamine (15.37 g, 60.80 mmol) and N,N- dimethylformamide dimethyl acetal (10. ImL, 76.00 mmol), suspended in ethanol (15O mL), is refluxed for 2 hours. The reaction mixture is evaporated in vacuo affording the title compound (18.6 g). 1H-NMR (400MHz, CDCl3) delta(ppm) 3.20 (s, 3H), 3.21 (s, 3H), 7.93 (s, IH), 8.48 (s, IH). LCMS: Rt 3.81 min (99.1%), m/z (APCI) 307 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,6-Dibromopyrazin-2-amine, its application will become more common.

Reference:
Patent; GALAPAGOS N.V.; WO2007/138072; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 762240-92-6

Add 20 mL of acetonitrile to a 50 mL round bottom flask.Add (3R)-3-[(1,1-dimethylethoxycarbonyl)-amino]-4-(2,4,5-trifluorophenyl)butanoic acid (3.32 g, 0.01 mol) and 3 -(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazole[4,3-alpha]piperazine hydrochloride (2.28 g, 0.01 mol),The temperature of the reaction system was cooled to 0 C with an ice salt bath, and 1-hydroxybenzotriazole (HOBT) (1.62 g, 0.012 mol) was added.1-ethyl-3-(3-dimethylaminopropyl)carbimide hydrochloride (EDC·HCl) (2.29 g, 0.012 mol),3 g of triethylamine was added dropwise, and the reaction was stirred at room temperature for 24 hours, and the reaction solution was washed with 3×20 mL of distilled water.The organic layer was dried over anhydrous magnesium sulfate for 1 hour, then filtered and evaporated. The desiccant was filtered off and concentrated to give 4.81 g of product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 762240-92-6.

Reference:
Patent; Zhejiang Haixiang Pharmaceutical Co., Ltd.; Zhejiang Pujian Pharmaceutical Co., Ltd.; Li Yongxin; Sheng Xiaoxia; Zhang Qunhui; Huang Guangdong; (21 pag.)CN103421011; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-01-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

The guanidine base was dissolved in anhydrousmethanol (2?3 mL/mmol) with methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (1 eq.) and refluxed for2 h under N2 atmosphere. The mixture was cooled toroom temperature, concentrated under reduced pressure,and purified by silica-gel column chromatography(Wako gel® C-200, 10percent methanol/chloroform) toafford series 3 (yield: 23?28percent). The spectral data of3a?3c were listed in the Supporting Information.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63744-22-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

11d (0.5 g, 2.8 mmol), 1a (0.8 g, 2.8 mmol), isopropanol (5.1 ml), and diisopropylethylamine (0.7 g, 5.6 mmol) were added to a 25 ml three-necked flask. The system was replaced with nitrogen for three times under stirring. The system was refluxed for 16 hours in 100 C oil bath. The system was cooled to 17 C, and concentrated to dryness under reduced pressure, purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/10 to 1: 3) to give light yellow solid Compound 11e (0.7 g, 99.5% purity, yield 72.6%). MS m/z 374.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromoimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; CHEN, Wenting; (53 pag.)EP3553065; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1422772-78-8 as follows. HPLC of Formula: C7H4BrN3O2

Ice bath,(COCl) 2 (7.5 mL) and DMF (0.4 mL)Was slowly added dropwise to a solution of 2-bromo-5H-pyrrolo [2,3-b] pyrazine-7-carboxylic acid (60%, 4.00 g, 8.26 mmol) in dichloromethane (150 mL)Reaction at room temperature for 2 h. Concentrated under reduced pressure,The residue was dissolved in dichloromethane (120 mL)Cyclobutylamine (2.2 mL, 26 mmol) and triethylamine were added(2.4 mL) was added and the reaction was carried out overnight. The reaction was quenched with water (150 mL)Dichloromethane (150 mL x 3), and the organic layer was dried over anhydrous Na2SO4, (Eluent: Cl2CH2 / MeOH (v / v) = 30/1) to give 1.20 g of a tan solid Rate: 49.0%.

According to the analysis of related databases, 1422772-78-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6966-01-4, A common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4- (PYRROLIDIN-1-YLSULFONYL) phenylboronic acid (0.33 g, 1.29 mmol), methyl 3-AMINO-6- bromopyrazine-2-carboxylate (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. CLIENT. Soc. 1949, 2798), K3PO3 (3 M, 1.1 ML, 3.2 mmol), and Pd (dppf) C12 (0.044 g, 54 , UMOL) were suspended in ethylene glycol dimethyl ether/water (1.5 : 0.5 mL) and heated in a microwave oven at 160 C for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient to give 0.96 g (82% yield) of the title compound: MS (ES) NAL, Z 363 (M++1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, belongs to pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 24241-18-7, COA of Formula: C4H3Br2N3

To a solution of 3,5-dibromopyrazin-2-amine (2.00 g, 7.91 mmol) in THF (24 mL)were added triethylamine (3.3 mL, 24 mmol), cuprous iodide (151 mg, 0.79 mmol) andPd(PPh3hCh (561 mg, 0.79 mmol). The mixture was cooled to -5 oc under nitrogen protection,then trimethylsilylacetylene (1.07 mL, 7.50 mmol) was dropwised slowly into the mixture. Afterthe addition, the mixture was warmed to 0 oc and stirred for 1.5 h. The mixture was concentratedin vacuo to remove the solvent and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 511) to give the title compound as black oil (42 mg, 94 %).MS (ESI, pos. ion) m/z: 272.00 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 8.04 (s, lH), 5.14 (s, 2H), 0.30 (s, 9H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

51171-02-9, name is Methyl 3-Bromo-2-pyrazinecarboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C6H5BrN2O2

(B) Methyl 2-phenylamino-3-pyrazine carboxylate: A mixture of 9.5 g. of methyl 2-bromo-3-pyrazine carboxylate, 8.2 g. of aniline, 0.5 g. of p-toluene sulfonic acid and 100 ml. of water was stirred and refluxed for two hours. The reaction mixture was poured on ice, extracted with ethyl acetate, the organic extracts were dried and concentrated to yield an oil. The crude residue was eluted on a silica gel column with ethyl acetate-hexane (1:2) yielding the product of this example as a yellow solid, m.p. 72-75 C.

The synthetic route of 51171-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US4680297; (1987); A;; ; Patent; Schering Corporation; US4680298; (1987); A;; ; Patent; Schering Corporation; US4740511; (1988); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem